The learning curve on these phones is substantial. I have had one since june of 2007 when I picked up a Mogul, I went to the Touch in August of 2008 and to the TP the weekend It came out.
Perhaps you are right that that these phones should work out of the box and they mostly do work OK, we just like to play with them and this does cause some confusion. The I phone only works with the certified apps and all of them must be bought. Our TP is so configurable it really is beyond belief.
Mine sync's over the air with corporate email and updates my calendar connected all the time, It check my three pop 3 email accounts evey hour. I use the GPS in google map, live search and telenav at times each week. I surf the net for work and for fun and I create word and excel documents when I'm waiting for a plane. I have even watched a movie on the plane. It takes really decent pictures organizes them on my laptop and transfers them their wirelessly. I even tether using bluetooth when wifi is not around on my laptop. The I phone will not do these things as well as my touch pro.
It takes trime to figure all these things out. I hope you choose the TP but if not take your time with the device and it will reward you well. Best of luck!!
Oh and it does these things for 40 bucks a month. Sero 500 and 10 bucks for telenav.
MOBO